I live in Bend and there are a few options for you...a lot more opens up with you having a sled. I haven't done to much backcountry skiing (just trying to get into it). I would call Pine Mountain Sports if you are looking for more information.
Anyhow, you can skin up Tumalo easily without having a sled. That is pretty much right next to Bachelor (park at Dutchman Flats Snowpark). Also from Dutchman's you can sled into some other places. Eventually you will need to park the sled (once you get to the wilderness boundary) and skin in to some areas. I've been to Ball Butte (you can park right next to it) and Broken Top it's a bit of a skin in to get there. I haven't been up South Sister, but I think you can make sled to the trailhead in the winter (I'm not sure about Middle and North). There's also Todd Lake from Dutchman's that you can either ski in or sled to.
I've never been to Tam McArther Rim, but I've heard a lot of great things about it. That's one area I need to hit this winter. I think it is about 6 miles from a snowpark, so having a snowmobile would be great for that trip. Check out Three Sisters Backcountry https://threesistersbackcountry.com/
for some info/photos. They just put in a yurt this season.
There is also some skiing at Paulina Lake...I've never been.
Anyhow...I hope that helps. We had some great snow, then it got pretty warm with snow/rain mix. Hopefully, though, that will create a solid base for the rest of the winter.